CA2068970C - Agent for transdermal administration containing ergoline derivatives - Google Patents

Agent for transdermal administration containing ergoline derivatives Download PDF

Info

Publication number: CA2068970C
Authority: CA; Canada
Prior art keywords: transdermal administration; lisuride; layer; acid; ergoline derivative
Prior art date: 1991-05-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002068970A

Other languages

English (en)

French (fr)

Other versions

CA2068970A1 (en

Inventor

Jutta Riedl

Clemens Gunther

Ralph Lipp

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Axxonis Pharma AG

Original Assignee

NeuroBiotec GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-05-18

Filing date

1992-05-19

Publication date

2005-09-27

1992-05-19 Application filed by NeuroBiotec GmbH filed Critical NeuroBiotec GmbH

1992-05-19 Priority to CA002068970A priority Critical patent/CA2068970C/en

1993-11-20 Publication of CA2068970A1 publication Critical patent/CA2068970A1/en

2005-09-27 Application granted granted Critical

2005-09-27 Publication of CA2068970C publication Critical patent/CA2068970C/en

2012-05-19 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 title claims abstract description 29
-1 lisuride Chemical class 0.000 claims abstract description 21
239000003961 penetration enhancing agent Substances 0.000 claims abstract description 19
BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 claims abstract description 16
229960003587 lisuride Drugs 0.000 claims abstract description 16
239000003937 drug carrier Substances 0.000 claims abstract 2
239000010410 layer Substances 0.000 claims description 22
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 20
230000001225 therapeutic effect Effects 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 11
239000000853 adhesive Substances 0.000 claims description 9
239000011241 protective layer Substances 0.000 claims description 9
239000008177 pharmaceutical agent Substances 0.000 claims description 8
239000004821 Contact adhesive Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
235000013772 propylene glycol Nutrition 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 6
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
FCRJELOYDVBTGW-ILZDJORESA-N 3-[(6ar,9s,10ar)-7-propyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)CCC)NC(=O)N(CC)CC)=C3C2=CNC3=C1 FCRJELOYDVBTGW-ILZDJORESA-N 0.000 claims description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
229950007140 proterguride Drugs 0.000 claims description 5
229960004558 terguride Drugs 0.000 claims description 5
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 4
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 claims description 3
SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 3
239000011703 D-panthenol Substances 0.000 claims description 3
235000004866 D-panthenol Nutrition 0.000 claims description 3
239000005639 Lauric acid Substances 0.000 claims description 3
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235000014113 dietary fatty acids Nutrition 0.000 claims description 3
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NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
239000005642 Oleic acid Substances 0.000 claims description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
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150000002367 halogens Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
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235000010446 mineral oil Nutrition 0.000 claims description 2
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ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
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239000000243 solution Substances 0.000 description 14
239000000725 suspension Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
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230000036470 plasma concentration Effects 0.000 description 7
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VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
229940052760 dopamine agonists Drugs 0.000 description 4
239000003136 dopamine receptor stimulating agent Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
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238000003756 stirring Methods 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
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229920002313 fluoropolymer Polymers 0.000 description 2
239000004811 fluoropolymer Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
239000013464 silicone adhesive Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
206010006298 Breast pain Diseases 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
102000006835 Lamins Human genes 0.000 description 1
108010047294 Lamins Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
208000006662 Mastodynia Diseases 0.000 description 1
241000489861 Maximus Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
102000003946 Prolactin Human genes 0.000 description 1
108010057464 Prolactin Proteins 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
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239000012752 auxiliary agent Substances 0.000 description 1
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150000001733 carboxylic acid esters Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
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229920003086 cellulose ether Chemical class 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
229940031769 diisobutyl adipate Drugs 0.000 description 1
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229940031569 diisopropyl sebacate Drugs 0.000 description 1
XFKBBSZEQRFVSL-UHFFFAOYSA-N dipropan-2-yl decanedioate Chemical compound CC(C)OC(=O)CCCCCCCCC(=O)OC(C)C XFKBBSZEQRFVSL-UHFFFAOYSA-N 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000009826 distribution Methods 0.000 description 1
LLRANSBEYQZKFY-UHFFFAOYSA-N dodecanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCC(O)=O LLRANSBEYQZKFY-UHFFFAOYSA-N 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
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150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
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150000002576 ketones Chemical class 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
230000007775 late Effects 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000012528 membrane Substances 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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230000001717 pathogenic effect Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
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150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
238000007789 sealing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000028327 secretion Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches

Landscapes

Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Dermatology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA002068970A 1991-05-18 1992-05-19 Agent for transdermal administration containing ergoline derivatives Expired - Fee Related CA2068970C (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002068970A CA2068970C (en)	1991-05-18	1992-05-19	Agent for transdermal administration containing ergoline derivatives

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DEP4116912.3		1991-05-18
DE4116912A DE4116912A1 (de)	1991-05-18	1991-05-18	Mittel zur transdermalen applikation enthaltend ergolin-derivate
CA002068970A CA2068970C (en)	1991-05-18	1992-05-19	Agent for transdermal administration containing ergoline derivatives

Publications (2)

Publication Number	Publication Date
CA2068970A1 CA2068970A1 (en)	1993-11-20
CA2068970C true CA2068970C (en)	2005-09-27

Family

ID=6432298

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002068970A Expired - Fee Related CA2068970C (en)	1991-05-18	1992-05-19	Agent for transdermal administration containing ergoline derivatives

Country Status (14)

Country	Link
US (1)	US5399355A (de)
EP (2)	EP0538433B1 (de)
JP (1)	JP3725153B2 (de)
AT (2)	ATE311862T1 (de)
AU (1)	AU1637792A (de)
CA (1)	CA2068970C (de)
DE (3)	DE4116912A1 (de)
DK (1)	DK1027889T3 (de)
ES (2)	ES2251936T3 (de)
HU (1)	HUT64227A (de)
IE (1)	IE921586A1 (de)
NO (1)	NO930148D0 (de)
PT (1)	PT100492B (de)
WO (1)	WO1992020339A1 (de)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2161004C (en) *	1993-04-20	2004-10-26	Wilfried Fischer	Active ingredient patch
DE19626621A1 (de) *	1996-07-02	1998-01-08	Hexal Ag	Pflaster zur transdermalen Anwendung von Pergolid
US5837289A (en) *	1996-07-23	1998-11-17	Grasela; John C.	Transdermal delivery of medications using a combination of penetration enhancers
US5900249A (en) *	1998-02-09	1999-05-04	Smith; David J.	Multicomponent pain relief topical medication
FR2793890B1 (fr)	1999-05-19	2002-01-18	France Telecom	Boitier d'acces a une ou plusieurs fibres optiques dans un cable tendu
DE10033853A1 (de) *	2000-07-12	2002-01-31	Hexal Ag	Transdermales therapeutisches System mit hochdispersem Siliziumdioxid
US20070243240A9 (en) *	2000-08-24	2007-10-18	Fred Windt-Hanke	Transdermal therapeutic system
DE10066158B4 (de) *	2000-08-24	2007-08-09	Neurobiotec Gmbh	Verwendung eines transdermalen therapeutischen Systems zur Behandlung des Restless-Legs-Syndroms
DE10053397A1 (de)	2000-10-20	2002-05-02	Schering Ag	Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen
DE10064453A1 (de) *	2000-12-16	2002-07-04	Schering Ag	Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen
EP1390383B1 (de) *	2001-05-11	2012-02-29	Isis Pharmaceuticals, Inc.	Antisense-permeationsverstärker
DE10137082A1 (de) *	2001-07-28	2003-02-13	Hexal Ag	Matrixkontrolliertes transdermales therapeutisches System zur Anwendung von Pramiprexol und Ropinirol
DE10137162A1 (de) *	2001-07-30	2003-02-20	Hexal Ag	Matrixkontrolliertes transdermales therapeutisches System zur Anwendung von Pramiprexol und Ropinirol
US7241456B2 (en) *	2002-10-25	2007-07-10	Australian Importers Ltd.	Formulations for topical delivery of bioactive substances and methods for their use
US20070196452A1 (en) *	2004-06-07	2007-08-23	Jie Zhang	Flux-enabling compositions and methods for dermal delivery of drugs
US8741332B2 (en) *	2004-06-07	2014-06-03	Nuvo Research Inc.	Compositions and methods for dermally treating neuropathic pain
US8741333B2 (en) *	2004-06-07	2014-06-03	Nuvo Research Inc.	Compositions and methods for treating dermatitis or psoriasis
US20070196457A1 (en) *	2004-06-07	2007-08-23	Jie Zhang	Two or more volatile solvent-containing compositions and methods for dermal delivery of drugs
US20070196453A1 (en) *	2004-06-07	2007-08-23	Jie Zhang	Two or more non-volatile solvent-containing compositions and methods for dermal delivery of drugs
US8907153B2 (en)	2004-06-07	2014-12-09	Nuvo Research Inc.	Adhesive peel-forming formulations for dermal delivery of drugs and methods of using the same
US20070280972A1 (en) *	2006-04-25	2007-12-06	Zars, Inc.	Adhesive solid gel-forming formulations for dermal drug delivery
DE102006048130A1 (de) *	2006-10-06	2008-04-10	Axxonis Pharma Ag	Transdermales therapeutisches System mit zweiphasigem Freisetzungsprofil
US20090239894A1 (en) *	2008-03-20	2009-09-24	Bjorn Schurad	Stabilized aqueous solutions of ergoline compounds

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3333240A1 (de) *	1983-09-12	1985-03-28	Schering AG, 1000 Berlin und 4709 Bergkamen	Mittel zur transdermalen applikation von arzneimittelwirkstoffen
KR920010392B1 (ko) *	1984-03-01	1992-11-27	산도즈 아크리엔 게젤샤프트	경피투여용 약학 조성물의 제조방법
US4883669A (en) *	1985-02-25	1989-11-28	Rutgers, The State University Of New Jersey	Transdermal absorption dosage unit for estradiol and other estrogenic steroids and process for administration
EP0208417A3 (de) *	1985-06-12	1989-09-06	SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu	Verwendung von 1-(8alpha-Ergolinyl)-3,3-diethylureaderivaten zur Behandlung von Endometritis
US4782063A (en) *	1987-05-11	1988-11-01	Eli Lilly And Company	Ergoline esters useful as serotonin antagonists
US4835159A (en) *	1987-05-11	1989-05-30	Eli Lilly And Company	Ergoline esters useful as serotonin antagonists
US5252335A (en) *	1989-07-12	1993-10-12	Cygnus Therapeutic Systems	Transdermal administration of lisuride
US5229129A (en) *	1989-07-12	1993-07-20	Cygnus Therapeutic Systems	Transdermal administration of lisuride

1991
- 1991-05-18 DE DE4116912A patent/DE4116912A1/de not_active Ceased
1992
- 1992-05-14 HU HU9300125A patent/HUT64227A/hu unknown
- 1992-05-14 EP EP92909703A patent/EP0538433B1/de not_active Expired - Lifetime
- 1992-05-14 ES ES00250117T patent/ES2251936T3/es not_active Expired - Lifetime
- 1992-05-14 ES ES92909703T patent/ES2219639T3/es not_active Expired - Lifetime
- 1992-05-14 DE DE59210003T patent/DE59210003D1/de not_active Expired - Lifetime
- 1992-05-14 WO PCT/DE1992/000400 patent/WO1992020339A1/de not_active Ceased
- 1992-05-14 JP JP50914192A patent/JP3725153B2/ja not_active Expired - Fee Related
- 1992-05-14 EP EP00250117A patent/EP1027889B8/de not_active Expired - Lifetime
- 1992-05-14 AT AT00250117T patent/ATE311862T1/de not_active IP Right Cessation
- 1992-05-14 DE DE59209996T patent/DE59209996D1/de not_active Expired - Fee Related
- 1992-05-14 AT AT92909703T patent/ATE264679T1/de not_active IP Right Cessation
- 1992-05-14 DK DK00250117T patent/DK1027889T3/da active
- 1992-05-15 PT PT100492A patent/PT100492B/pt not_active IP Right Cessation
- 1992-05-18 AU AU16377/92A patent/AU1637792A/en not_active Abandoned
- 1992-05-19 CA CA002068970A patent/CA2068970C/en not_active Expired - Fee Related
- 1992-07-01 IE IE158692A patent/IE921586A1/en not_active Application Discontinuation
1993
- 1993-01-15 NO NO930148A patent/NO930148D0/no unknown
- 1993-03-30 US US08/040,393 patent/US5399355A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IE921586A1 (en)	1992-11-18
HUT64227A (en)	1993-12-28
PT100492A (pt)	1993-10-29
DK1027889T3 (da)	2006-04-18
AU1637792A (en)	1992-11-19
DE59209996D1 (de)	2004-05-27
ATE264679T1 (de)	2004-05-15
ES2251936T3 (es)	2006-05-16
JPH06500126A (ja)	1994-01-06
JP3725153B2 (ja)	2005-12-07
ES2219639T3 (es)	2004-12-01
EP0538433B1 (de)	2004-04-21
DE4116912A1 (de)	1992-11-26
US5399355A (en)	1995-03-21
EP1027889B8 (de)	2006-07-05
CA2068970A1 (en)	1993-11-20
EP1027889B1 (de)	2005-12-07
EP0538433A1 (de)	1993-04-28
HU9300125D0 (en)	1993-04-28
EP1027889A2 (de)	2000-08-16
NO930148L (no)	1993-01-15
PT100492B (pt)	1999-06-30
EP1027889A3 (de)	2001-01-24
DE59210003D1 (de)	2006-01-12
WO1992020339A1 (de)	1992-11-26
NO930148D0 (no)	1993-01-15
ATE311862T1 (de)	2005-12-15

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Legal Events

Date	Code	Title	Description
1999-03-31	EEER	Examination request
2011-05-19	MKLA	Lapsed